Sometime around the middle of April 1804, a slave named John Freeman wrote a letter to the president of the United States. Freeman, technically owned by a Maryland doctor, William Baker, had been contracted to work for Thomas Jefferson, who engaged him to serve in the White House and accompany Jefferson on trips to Monticello.

Now, Freeman was writing because he wanted the president to buy him outright.

"I am sorye to trubel you with a thing of this kind," he began, saying he felt obliged to do so because "I have been foolish anufe to in gage myself to Melindar."

The letter was an extraordinary feat of persuasion, heartfelt but also artful. Freeman, promising to serve Jefferson faithfully, went on to ask whether the president might even be "so good as to keep us [both]" -- that is, purchase a female slave named Melinda Colbert. On their trips to Virginia, Freeman had become enamored of Colbert, a niece of Sally Hemings who belonged to Jefferson's daughter Maria and her husband. Maria died that month, and the two slaves feared Melinda would be sold away.

The letter was one among numerous acts of resourcefulness and initiative that would result, years later, in John Freeman's being purchased and owned by not one U.S. president, but two. He would marry his beloved Melinda; gain his freedom; and, not least, purchase a piece of property on K Street in Northwest Washington, between 18th and 19th streets. There Freeman would establish a home for her and their children, taking his place among a unique, now largely forgotten community of free black residents with ties to U.S. presidents such as Jefferson, James Madison and George Washington.

In the ensuing years Freeman'sneighborhood became home to by a striking number of freed slaves who also had been owned by presidents. In the middle of the 19th century, the community included men and women whose start in life was about as disadvantaged as a human being's could be, but who, through drive and intellect and that classic Washington ingredient -- influential connections -- were able to improve their prospects. They would socialize together, work together and acquire property that in some cases would allow descendants to enjoy lives easier than theirs had been.

"Wouldn't you like to have had a piece of property on K Street?" says Beth Taylor, an independent scholar and former director of education at Montpelier, the historic home of James Madison. While researching Madison slaves, Taylor has become fascinated by this area, once home to what she calls Washington's "first families of color." Their life stories testify to the bonds between freed blacks in antebellum Washington, and remind us that a number of early American presidents did indeed own other human beings.

"As I do more research on the neighborhood, I wouldn't be at all surprised if I found descendants of slaves who worked for Tyler, Polk, Taylor, Jackson,"Taylor says. "These were all presidents, like Jefferson and Madison, who had slaves working for them in the White House."

In the early days of the union, she explains, presidents needed 10 or12 people to run the domestic side of the White House. The staff was often a mix of whites, free blacks and slaves, some from their own plantations, some purchased in the city and some, like Freeman, hired from other masters.

"One aspect of it that always strikes me is how these statesmen . . . had a real tendency to talk about the slavery problem, the slavery issue," Taylor reflects. "There was this lack of understanding on their part. . . . This is not the slavery problem. These are people enslaved."

Path to freedom

The neighborhood in which many of the former White House slaves settled is the downtown area -- now office buildings, retail stores and forgettable corporate architecture -- roughly bordered by K and M streets running east and west, and 15th and 21st running north and south. Back then, Taylor says, it would have been mostly residential, with modest frame and brick dwellings and stables. It was close to the city's action -- Lafayette Square, Pennsylvania Avenue, the White House -- but far enough away to be affordable.

Freeman was one of the first to settle there, but only after years of striving. In 1804, Jefferson did buy him for $400, agreeing to his Maryland master's promise that Freeman must receive his freedom in 1815.

The president declined to buy Melinda Colbert, saying there were too many servants "in idleness" at Monticello already, and "at Washington I prefer white servants, who when they misbehave can be exchanged." But she was able to remain at Monticello, hired out as a house servant to a resident free workman. Freeman could see her on visits. Though slaves could not legally marry, they considered themselves husband and wife, and began to have children.

Freeman, a man of ability, was described by one witness as being about 5-foot-7, "straight and well made" with a "very pleasing countenance." He was extremely well regarded. "Jefferson obviously valued him very highly," says Cinder Stanton, a senior historian at Monticello.

But by 1809, two things had happened: Melinda had been given her freedom, enabling her to move to Washington. Ironically, however, Jefferson's term as president was ending, and a Virginia law stating that freed slaves must depart the state within a year of being freed meant it would be risky for her to return to Monticello, as her husband was expected to do. There was only one remedy.

"Sir i am sory to say or do any thing to distress you," Freeman wrote in another letter to Jefferson. In it, he said he was willing to go to Monticello, but pointedly noted, "I shall be oblige to leave hir and the children."

The upshot was that Jefferson agreed to sell Freeman to James Madison, the incoming president. To arrive at a sales price, he calculated what he had paid for Freeman, reckoned how much time was left before 1815, and came up with a sum -- $231.81 -- that Taylor calls "so Jeffersonian" in its mathematical precision.

Freeman's life now intertwined with that of Paul Jennings, a boy of 10 who had been born into slavery at Montpelier and now came to Washington with Madison; in the White House, Freeman was a mentor to him. They were footmen, Taylor says, which means they served in the dining room, acted as messengers, and did whatever else was needed. Melinda, a free woman, did sewing for the Madisons, for which she was paid. She and Freeman lived on the White House grounds. Then in 1815, James Madison duly granted John Freeman his freedom.

Integrated neighborhood

Freeman was clearly preparing for this moment. Around this time, he and a friend bought $400 worth of belongings, including a cart and carriage, horses, and furniture. "Obviously he's getting ready to establish his own household," Taylor says. By 1821, Stanton has discovered, he had bought the lot on K Street, and by 1825 there was a two-story brick dwelling on it.

Freeman worked as a waiter at Gadsby's Hotel and as a messenger at the State Department. In this he was like many peers, who found that low-level federal government work was, as Taylor puts it, "about the highest that a free black could aspire to."

"I would say that all that these black men accomplished was in a pervasive atmosphere of impediments -- legal impediments, social impediments, psychological impediments," Taylor says.

One notable aspect of the neighborhood Freeman selected was that it was integrated. In 1840, in the city of Washington, whites outnumbered blacks, and free blacks now outnumbered slaves. It would be a far cry to say relations were harmonious. The Nat Turner rebellion of 1831 had made whites nervous, and in 1835, whites in the District made their fears known in what was called the Snow Riot. There were Black Codes, not always enforced, restricting the movement of black residents.

Even so, Taylor says, extreme, Jim Crow-type segregation was not yet the norm.

"People always assume that we've had this step-by-step advancing of race relationships, but that's far from true," Taylor says. "They've gone up and down, up and down. In this period I'm talking about, starting in the late 1840s, people weren't all that uptight" about the race of their neighbor.

Freeman was joined by other free African Americans. The household of John Brent was on the corner of L and 18th, where a Borders bookstore is now, and by 1854 Paul Jennings had settled beside him. Like Freeman, Jennings earned a home of his own through extraordinary determination. After Madison's tenure, Jennings moved back to Montpelier, then returned to Washington with Dolley after Madison's death. Dolley, who was having financial difficulties, had promised to free Paul in her will, but he came to doubt this would happen. Taking matters into his own hands -- and taking advantage of social connections -- he arranged for Daniel Webster, through an intermediary, to lend him his purchase price of $200, Taylor says. He worked off the debt and proceeded to acquire two houses. He would later give Dolley Madison small sums of money.

Neighborhood of notables

Nor were they the only neighborhood residents with presidential connections. Just a few blocks away, in properties on M and L streets, lived William, Charles and Colbert Syphax, free brothers who belonged to what would be one of the city's most elite black families. It is Syphax family tradition -- and generally not disputed -- that these Syphaxes were the grandsons of no less than George Washington Parke Custis and a slave. Custis was himself the grandson of Martha Washington, giving the Syphaxes ties of both blood and bond to Mount Vernon, where some forebears had worked. Some Syphaxes settled on the Virginia side of the river, and rose to prominence there.

The reason these three settled in Washington may be simple: jobs. William worked for the Department of the Interior, where he achieved the title of "Chief Messenger"; he was also a community leader in education for black children. Charles worked in the pension office with Paul Jennings.

Despite living in integrated surroundings, these residents, Taylor says, clearly were made to feel unwelcome in important places, like churches. So residents established black churches to have a place to worship -- and gather -- privately. Many were involved in efforts to help other slaves. John Freeman and his sons, Stanton says, were active in efforts to raise money to help slaves buy their freedom.

In fact, it was from this neighborhood that an ambitious slave escape was plotted; in 1848, white Northern abolitionists arranged for 77 slaves to be stowed in a schooner, the Pearl, bound for the North. Assisting them were Paul Jennings; John Brent; and Brent's wife, Elizabeth Edmonson, who had enslaved siblings aboard.

The attempt failed, and so dangerous and secret was the endeavor that some of Paul Jennings's descendants did not know about it until fairly recent published accounts appeared. "The Pearl story was new to me," says Hugh Alexander, a Maryland resident descended from Jennings, whose late mother, a family historian, kept his daguerreotype on the wall.

Eventually, other former Montpelier slaves moved to the community. "That cannot be a coincidence," Taylor says. One of them, Ben Stewart, had been sold to an owner in Georgia, then found his way back to Washington and got a job as a guide at the U.S. Capitol. In time, many residents would marry neighbors, and properties stayed in families for generations.

Now, the houses are mostly or completely gone, and with it the known fate of the Freeman line. According to Cinder Stanton, John and Melinda -- who did legally marry -- had 10 children, one of whom, Benjamin, worked as a clerk in the patent office. Melinda outlived John, who died in 1839. Her 1857 will was witnessed by their longtime friend, Paul Jennings.

To date, Stanton has been unable to find living descendants, but she knows that one grandson, John Freeman Shorter, fought in the Civil War. Shorter rose to become a lieutenant of the 55th Massachusetts, together, coincidentally enough, with two other black men with Monticello ties.

According to the account of a white officer, this John Freeman was a well-educated man "with every soldierly quality, from scrupulous neatness to unflinching bravery." Though wounded, he re-mustered, then in 1865 set out for Ohio, where his fiancee was living. He contracted smallpox en route, and died. In that sense he was less fortunate than his grandfather, who went through so much to join a community of people who had endured the same extremes he had, and was able to live out his days in the company of the woman for love of whom he had the temerity to write a president. Twice.

Independent historian Beth Taylor will be speaking about these people and events in history at a lecture and reception on Feb. 17 at 6 p.m. at the National Center for White House History (formerly Decatur House) on Lafayette Square. E-mail basher@montpelier.org or call 540-672-2728, Ext. 109, to RSVP.